Diazomethane → HCID 22402960, compound

HRID 1031028Notes

Reaction equation

HRID 1031028 reaction equation
[C:1]([C:4]([NH:9][C:10]([C:12]1[C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([CH3:25])=[N:15][N:16]2[CH3:24])=[O:11])([CH3:8])[CH:5]([CH3:7])[CH3:6])(=[O:3])[NH2:2].[N+](=[CH2:28])=[N-]>CN(C)C=O>[C:1]([C:4]([NH:9][C:10]([C:12]1[C:20]([C:21]([O:23][CH3:28])=[O:22])=[CH:19][CH:18]=[C:17]2[C:13]=1[C:14]([CH3:25])=[N:15][N:16]2[CH3:24])=[O:11])([CH3:8])[CH:5]([CH3:6])[CH3:7])(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 22402981HCID 22402981, compound

Product 1

HCID 22402960HCID 22402960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]1,3-dimethyl-1H-indazole-5-carboxylic acid (0.720 g, 2.07 mmol) in dry dimethylformamide is treated with sufficient ethereal diazomethane to give a permanent yellow color. The excess diazomethane is quenched with acetic acid, and the reaction mixture is concentrated in vacuo. The resultant residue is chased 2 times with xylene recrystallized from 50% aqueous methanol to give the title product as a white solid, mp 221°-222° C.

Workup

  1. customto give a permanent yellow color
  2. customThe excess diazomethane is quenched with acetic acid
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. customrecrystallized from 50% aqueous methanol

Sources & evidence

ORD record
ord-15fc17ff6d2a41af859a0395f613fd9c
Source dataset
uspto-grants-1992_04
Patent number
US05108485

Reaction notes

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